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23. Grandmaster B (Bud Bundy)

Image via Columbia Pictures Television

As seen on: Married...With Children (Fox)Portrayed by: David Faustino

Behind Al Bundy, Bud Bundy is Married... With Children's second-best character. His failures at getting girls are always brutal, crushing, and hilarious—for most of the show he couldn't even score a single date.

Nothing changed when he introduced his still-non-girl-getting alter ego, Grandmaster B. His profile is your worst nightmare: a five-foot-tall, pasty white dude wearing Chuck D gear and rapping like a knockoff Vanilla Ice. Worse, this was inspired by actor David Faustino's real-life mistake in pursuing a rap career.

Predictably, Grandmaster B flopped with the ladies, and with us. Thankfully, the writers eventually made him drop the mic, in the trash.